A diner with a green roof and a red barn in the background.

Spencertown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Spencertown vacation rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,108 reviews)
"Clean & comfortable stay"
United States
Robert
$108 nightly
The price is $120
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
Exterior

2. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (171 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
$133 nightly
The price is $150
Sep 6 - Sep 7
Total with taxes and fees
Micosta Leisure Inn
Private kitchen

3. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Michael’s place in Great Barrington MA was incredible. It was clean, very well appointed, affordable and so quiet. It is also very close to numerous restaurant options and grocery stores. I thought the place was very cozy and so comfortable. This was a stopping off point for me so I unfortunately was not able to stay longer. Next time I am Great Barrington I will definitely look up Michael’s place. Thank you Michael."
United States
Paul J.
$148 nightly
The price is $165
Sep 8 - Sep 9
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
Property grounds

4. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (13 reviews)
"This property is really nice. House is beautiful and the man cave is a nice addition. Wish we were there long enough to use it."
United States
Jen R.
$307 nightly
The price is $344
Sep 20 - Sep 21
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Room

5. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
$172 nightly
The price is $193
Sep 2 - Sep 3
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Property grounds

6. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
$126 nightly
The price is $141
Sep 3 - Sep 4
Total with taxes and fees
All the comforts of home
Terrace/patio

7. BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$308 nightly
The price is $347
Sep 2 - Sep 3
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Dining

8. Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
$308 nightly
The price is $347
Sep 2 - Sep 3
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Property grounds

9. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (58 reviews)
"Loved the place and would love to come back. "
United States
Georgine
$118 nightly
The price is $132
Sep 6 - Sep 7
Total with taxes and fees
All comforts of home
Interior

10. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
$286 nightly
The price is $319
Sep 3 - Sep 4
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Private kitchen

11. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
$238 nightly
The price is $242
Sep 10 - Sep 11
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
Interior

12. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
$270 nightly
The price is $302
Sep 8 - Sep 9
Total with taxes and fees
Cozy Riverside Berkshires Retreat
Dining

13. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Terrace/patio

14. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (3 reviews)
"Very nice. Will rent again!"
United States
Kathy A.
$328 nightly
The price is $367
Sep 7 - Sep 8
Total with taxes and fees
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Pool

15. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.0 out of 10, Wonderful, (4 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
$342 nightly
The price is $383
Sep 2 - Sep 3
Total with taxes and fees
Hudson NY’S Country Serenity Guest Suite.
Exterior detail

16. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
$712 nightly
The price is $797
Sep 2 - Sep 3
Total with taxes and fees
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Living area

17. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
$224 nightly
The price is $227
Sep 14 - Sep 15
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
Room

18. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (8 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$181 nightly
The price is $203
Sep 2 - Sep 3
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Outdoor dining

19. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (25 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
$320 nightly
The price is $358
Sep 2 - Sep 3
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Private kitchen

20. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
$330 nightly
The price is $368
Sep 6 - Sep 7
Total with taxes and fees
Home in Great Barrington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Spencertown Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"outstanding"
ROBERT 4-night trip
Posted 1 hour ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

Find out more about Spencertown

Everything you need to know about Spencertown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Spencertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Spencertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Spencertown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Spencertown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Spencertown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $120 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Spencertown rentals

At Expedia, we put the best Spencertown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Spencertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Spencertown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Spencertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Spencertown?

Yes, you can find vacation rentals close to popular points of interest in Spencertown, or you can go with a secluded option if you want a relaxing place to stay.

What's the top vacation rental that Spencertown has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental near Spencertown is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Spencertown?

Expedia has 3 vacation rentals for your stay in Spencertown.

What’s there to see and do in Spencertown?

Explore the area and family-friendly sights such as Bousquet Ski Area, or get out into nature at a spot like Berkshire Botanical Garden. Norman Rockwell Museum and Catamount Aerial Adventure Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Spencertown like?

A vacation rental is a private property you can book for a couple of days or more in Spencertown. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.